Planning Shouldn't be a Chore but an Exploration

Don’t skip planning during uncertain times – here’s the right framing to help you execute flexibly

You often hear me talk about how, to achieve big goals during uncertainty, you need to plan ahead but be flexible in your execution to adapt to all the challenges that will be thrown at you.

This quote is attributed to US President Dwight D. Eisenhower who in the 1950s referenced an army saying as: “Plans are useless, but planning is essential.”

What does that even mean? – I hear you ask. Why waste time on writing plans if they are useless anyway?

Now, unlike some of you reading this, I have never been in any army, but we all know business strategists love to repurpose war metaphors. So here goes the reason for my opening.

When trying to achieve something great in uncertain times, no matter how much you plan ahead, you will find yourself in scenarios that are rather different from what you planned for. You can easily end up feeling like you’re just treading water.

Even if there isn’t a sudden credit crunch (2008) or a crushing global pandemic derailing the business, life moves fast and as much as we are all the main characters of our own lives, so are all the other people running our competitors or buying our products.

Don’t get me wrong. I know how many entrepreneurs and directors feel about business plans: an away day, discussions, put something in a pretty document, put it in the drawer, forget about it for 6 months or a year and just go about the daily running of the business or the department.

I get it. But even if you get swept up by the day-to-day whirlwind (Tariffs! Trade deals! Interest rates! Supplier or buyer bankruptcies!), the planning process itself is valuable and should not be looked at as a burden.

Since the pandemic, we’ve been talking more and more about the need to do scenario planning instead of relying on forecasts.

When things are this unpredictable, when the business environment changes this fast, forecasts become useless fast.

Scenario planning is your friend.

By going through the process of planning itself, you are forced to consider and explore different options and different potential actions, responses and outcomes. Thus, when suddenly faced with a new reality that is not in your favour, you will already have a very good understanding of your options. You will have tools in your arsenal that you can deploy instead of making quick decisions in a panic.

Just as importantly, you will be ready mentally as you would have thought through different scenarios and got clarity on your constraints and end goal.

I cannot emphasise this enough: It is important not to be wedded to any plan so much that you cling to it no matter what, or just freeze if one thing goes wrong and you are forced to deviate.

Here’s another quote, this time attributed to Winston Churchill: “the best generals are those who arrive at the results of planning without being tied to plans”.

Whether it was Churchill who said this or not (thanks, internet, for all the misattributions), I like this iteration of the concept even more as it is focused on the outcome.

Mark Carney, PM of Canada, former governor of the Bank of England, when talking about building resilience into the financial system and building in anti-fragility also quoted Eisenhower as above and added: “Assume the bad thing – make sure the system is there.”

It is important to think through what happens if the bad thing does happen.

Lots of senior people are being made redundant at the moment, or have decided to take advantage of how easy it has become to start a new business. So they take the plunge and set up on their own. If that is your path, I hope you are excited and optimistic. However, I hope you also consider what happens if things don’t work exactly as you would like and have some backup plans and alternatives you can pivot to.

Any business facing uncertainties should consider questions like:

• What’s your worst-case scenario? (Be brutally honest.)

• What and how can you mitigate?

• What’s your risk appetite?

• What are the alternatives?

Planning for the worst case goes against every instinct of forever optimists, like most entrepreneurs I know. But planning for the worst does not mean you are planning to fail.

Systems and Structures can help or hinder your ability to adapt and win.

Planning, thinking and taking action aren’t enough to keep going through uncertain times.

It is the systems in your business that you need to set up in a way that serves your goal, no matter what happens.

Not many startup founders can transition to the corporate CEO role partly because leading a large organisation is very different from the creative, chaotic, “we are all in this together” energy of a founding team. I am very fond of flexibility and don’t like much bureaucracy, but once there are more than a couple of handful of people in an organisation, structure and processes become necessary.

But this isn’t just about fast-growing startups. Established businesses can easily find themselves casualties